409092-97-3Relevant academic research and scientific papers
A way to highly enantiomerically enriched aza-Morita-Baylis-Hillman-type products
Utsumi, Naoto,Zhang, Haile,Tanaka, Fujie,Barbas III, Carlos F.
, p. 1878 - 1880 (2007)
(Chemical Equation Presented) Going Mannich: Difficult to synthesize β-amino carbonyl compounds bearing α-alkylidene groups have been prepared enantioselectively (up to 99% ee) by reaction of β-substituted α,β-unsaturated aldehydes and α-imino esters in t
List-Barbas-Mannich reaction catalyzed by modularly designed organocatalysts
Perera, Sandun,Sinha, Debarshi,Rana, Nirmal K.,Trieu-Do, Van,Zhao, John Cong-Gui
, p. 10947 - 10953 (2013)
The List-Barbas-Mannich reaction of ethyl (p-methoxyphenylimino)acetate (p-methoxyphenyl = PMP) with unmodified aldehydes or ketones catalyzed by modularly designed organocatalysts (MDOs) that are self-assembled from proline and cinchona alkaloid thiourea
Direct organocatalytic asymmetric Mannich-type reactions in aqueous media: One-pot Mannich-allylation reactions
Córdova, Armando,Barbas III, Carlos F.
, p. 1923 - 1926 (2003)
The first direct organocatalytic asymmetric Mannich-type reactions in aqueous media are demonstrated herein. L-Proline-catalyzed reactions in aqueous media to provide β-formyl substituted α-amino acid derivatives with excellent diastereoselectivities (dr
Pipecolic acid-catalyzed direct asymmetric Mannich reactions
Cheong, Paul Ha-Yeon,Zhang, Haile,Thayumanavan, Rajee,Tanaka, Fujie,Houk,Barbas III, Carlos F.
, p. 811 - 814 (2006)
Mannich reactions between aldehydes and N-p-methoxyphenyl-protected α-imino ethyl glyoxylate have been performed using (S)-pipecolic acid as catalyst. The reactions give both syn- and anti-products (dr = 1.4-2:1) with high enantioselectivities (>98% ee).
Diastereoselective Hydrolysis of Branched Malonate Diesters by Porcine Liver Esterase: Synthesis of 5-Benzyl-Substituted Cα-Methyl-β-proline and Catalytic Evaluation
Kotapati, Hari Kiran,Robinson, Jamarii D.,Lawrence, Daniel R.,Fortner, Kimberly R.,Stanford, Caleb W.,Powell, Douglas R.,Wardenga, Rainer,Bornscheuer, Uwe T.,Masterson, Douglas S.
, p. 3009 - 3016 (2017/06/06)
Malonate diesters with highly branched side chains containing a preexisting chiral center were prepared from optically pure amino alcohols and subjected to asymmetric enzymatic hydrolysis by Porcine Liver Esterase (PLE). Recombinant PLE isoenzymes have be
An enantiodivergent synthesis of Cα-methyl nipecotic acid analogues from δ-lactam derivatives obtained through a highly stereoselective cyclization strategy
Banerjee, Souvik,Vogel, Emily R.,Hinton, Daniel,Sterling, Michael,Masterson, Douglas S.
, p. 1292 - 1299 (2015/11/09)
A stereoselective and enantiodivergent strategy for the construction of δ-lactams is described. The strategy utilizes chiral malonic esters prepared from enantiomerically enriched mono esters of disubstituted malonic acid. A cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. The resulting δ-lactams are then converted into nipecotic acid analogues using straightforward transformations. The resulting nipecotic acid analogues proved capable organocatalysts in Mannich reactions.
Indoline-3-carboxylic acid derived organocatalysts for the anti-mannich reaction
Pietruszka, Joerg,Simon, Robert Christian
, p. 14534 - 14544 (2011/03/20)
Mannich type reactions of a preformed aldimine with various carbonyl compounds were investigated with a series of functionalised indoline derivatives as catalysts: indoline-3-carboxylic acid, the diphenylcarbinol analogue and O-protected silyl ether analo
Enantioselective organocatalytic mannich reactions with autocatalysts and their mimics
Wang, Xinbo,Zhang, Yongbo,Tan, Haibo,Wang, Yanchao,Han, Peng,Wang, David Zhigang
supporting information; experimental part, p. 2403 - 2406 (2010/07/08)
(Figure Presented) The Mannich reactions previously extensively investigated with organocatalysis of L-proline and other related small molecules were reinvestigated with detailed stereochemical analysis of their autocatalysis pathways, through employment
A solid-supported organocatalyst for highly stereoselective, batch, and continuous-flow mannich reactions
Alza, Esther,Rodriguez-Escrich, Carles,Sayalero, Sonia,Bastero, Amaia,Pericas, Miquel A.
experimental part, p. 10167 - 10172 (2010/04/05)
The fast and highly stereoselective Mannich reaction of aldehydes and ketones with the N-(p-meihoxyphenyl) ethyl glyoxylate imine catalyzed by polystyrene resins functionalized with (2S,4R)-hydroxyproline is reported. The effect of the nature of the linke
TRANS-3,5-DISUBSTITUTEDPYRROLIDINE: ORGANOCATALYST FOR anti-MANNICH REACTIONS
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Page/Page column 16; 25, (2010/11/27)
A compound of Formula I is disclosed, in which R is a substituent containing a hydrogen bond-forming atom within three atoms from the ring carbon to which the substituent is bonded; X is CH2, O, S or NR1, wherein R1 is a hydrocarbyl group or an amino-protecting group having one to about 18 carbon atoms; R2 is hydrido or a hydrocarbyl group containing one to about twelve carbon atoms; and R3 is hydrido or methyl, but both R2 and R3 are not hydrido when X is CH2 A molecule of Formula I and those in which R2 and R3 can both be hydrido (Formula X) functions as a catalyst in a Mannich reaction to asymmetrically form β-aminoaldehyde or β-aminoketone diastereomeric products having two chiral centers on adjacent carbon atoms and in which the anti-diastereomers are in excess over the syn-diastereomers. Methods for carrying out those syntheses are also disclosed.
